Acetyl chloride → (+/-)-1-BOC-4-acetyl-3-phenyl-piperazine

HRID 530626노트

반응식

HRID 530626 반응식
[C:1]1([CH:7]2[NH:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:27](Cl)(=[O:29])[CH3:28]>ClCCl.C(=O)(O)[O-].[Na+]>[C:16]([O:15][C:13]([N:9]1[CH2:10][CH2:11][N:12]([C:27](=[O:29])[CH3:28])[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

참가 물질

6

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 2735358Tert-butyl 3-phenylpiperazine-1-carboxylate

생성물 1

HCID 67083964(+/-)-1-BOC-4-acetyl-3-phenyl-piperazine수율 54%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

To a mixture of tert-butyl 3-phenylpiperazine-1-carboxylate (400 mg, 1.52 mmol) and triethyl amine (309 mg, 3.05 mmol) in dichloromethane (5 mL) was added acetyl chloride (156 mg, 1.98 mmol) at 0° C. After stirring for 3 h at room temperature, the reaction mixture was diluted with saturated sodium bicarbonate solution and dichloromethane. The aqueous part was extracted with dichloromethane and the combined organic part was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (20/1 dichloromethane/methanol) to afford 4-acetyl-3-phenyl-piperazine-1-carboxylic acid tert-butyl ester (250 mg, 54%). [M-BOC]H+=205.

후처리

  1. extractionThe aqueous part was extracted with dichloromethane
  2. dry with materialthe combined organic part was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (20/1 dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-5490e463d5c44e0786f3c839e3fc72c5
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353096B2

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